A diner with a green roof and a red barn in the background.

Spencertown Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Spencertown vacation rentals

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

1. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.4 out of 10, Exceptional, (189 reviews)
"Great stay"
United States
George
$113 nightly
The price is $127
Oct 20 - Oct 21
Total with taxes and fees
Micosta Leisure Inn
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,208 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
$113 nightly
The price is $126
Nov 16 - Nov 17
Total with taxes and fees
Berkshire Mountain Lodge
A camping setup with a metal chair and a table by a river in a forest.

3. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (16 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
$307 nightly
The price is $344
Oct 19 - Oct 20
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A wooden deck with a staircase leading to a covered porch area.

4. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (64 reviews)
"The room was sufficient to our needs. Didn’t realize it was a multi-unit property or that it was on the second floor."
United States
Douglas
$118 nightly
The price is $132
Oct 20 - Oct 21
Total with taxes and fees
All comforts of home
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

5. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
$203 nightly
The price is $206
Oct 18 - Oct 19
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
A wooden deck with a staircase leading to a covered porch area.

6. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
United States
Lori M.
$126 nightly
The price is $141
Oct 19 - Oct 20
Total with taxes and fees
All the comforts of home
A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

7. Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (4 reviews)
"This place was better than the photos. Everything was well planned out and extremely comfortable. The host was very attentive with great information about the area. Would definitely recommend."
United States
Lori S.
$304 nightly
The price is $343
Nov 2 - Nov 3
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

8. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (9 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
$148 nightly
The price is $165
Oct 25 - Oct 26
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

9. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
$170 nightly
The price is $190
Oct 18 - Oct 19
Total with taxes and fees
The Brooks Motel: Exceptional Suite
A spacious living room with a dining area, a kitchen, and a large window.

10. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
$222 nightly
The price is $225
Nov 9 - Nov 10
Total with taxes and fees
1800s Carriage house in Berkshires / Hudson Valley
A cozy living room with a sofa, a fireplace, and large windows.

11. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
$607 nightly
The price is $679
Oct 21 - Oct 22
Total with taxes and fees
Luxury Barn Near Hudson With New Private Sauna
A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

12. BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
$304 nightly
The price is $343
Nov 16 - Nov 17
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
A modern building with a wooden deck and a door.

13. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
$556 nightly
The price is $623
Oct 19 - Oct 20
Total with taxes and fees
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A staircase with a wooden handrail and a white wall with a light switch.

14. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
$253 nightly
The price is $282
Oct 26 - Oct 27
Total with taxes and fees
Leaf-Peeper Paradise in the Berkshires
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

15. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
$314 nightly
The price is $351
Oct 18 - Oct 19
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
A sandy beach with a lake and forest in the background.

16. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
$284 nightly
The price is $317
Nov 16 - Nov 17
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A two-story house with a balcony, a deck, and a view of the surrounding forest.

17. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (134 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
$509 nightly
The price is $570
Oct 18 - Oct 19
Total with taxes and fees
Gorgeous Mountain Views Retreat: Family & Nature
A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

18. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.2 out of 10, Wonderful, (5 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
$340 nightly
The price is $381
Oct 18 - Oct 19
Total with taxes and fees
Hudson NY’S Country Serenity Guest Suite.
A backyard with a fire pit, wooden deck, and string lights.

19. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (4 reviews)
"Enjoyed our 2 night stay, everything was clean and worked smoothly. The hot tub and couch were the favorites, also enjoyed the coffee maker very much. Would highly recommended staying here!"
United States
Ross O.
$326 nightly
The price is $365
Oct 19 - Oct 20
Total with taxes and fees
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

20. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
$578 nightly
The price is $646
Oct 20 - Oct 21
Total with taxes and fees
Secluded Family Home in Serene Stockbridge Woods
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Spencertown Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"
Hope 1-night trip
Posted 11 hours ago
The Red Lion Inn

Find out more about Spencertown

Everything you need to know about Spencertown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Spencertown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Spencertown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Spencertown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Spencertown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Spencertown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $126 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Spencertown rentals

At Expedia, we put the best Spencertown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Spencertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Spencertown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Spencertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Spencertown?

Yes, you can find vacation rentals close to popular points of interest in Spencertown, or you can go with a secluded option if you want a relaxing place to stay.

What's the top vacation rental that Spencertown has to offer?

Catskill Cottage Walk to Downtown & River Views: This vacation home rental near Spencertown offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Spencertown?

Expedia has 3 vacation rentals for your stay in Spencertown.

What’s there to see and do in Spencertown?

Explore the area and family-friendly sights such as Bousquet Ski Area, or get out into nature at a spot like Berkshire Botanical Garden. Norman Rockwell Museum and Catamount Aerial Adventure Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Spencertown like?

A vacation rental is a private property you can book for a couple of days or more in Spencertown. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for small groups.